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C9137

Sigma-Aldrich

Cordycepin 5′-triphosphate sodium salt

≥95%

Synonyme(s) :

3′-dATP, 3′-deoxy-ATP, 3′-Deoxyadenosine 5′-triphosphate

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About This Item

Formule empirique (notation de Hill):
C10H16N5O12P3
Numéro CAS:
71997-32-5
Poids moléculaire :
491.18
Numéro MDL:
MFCD00057015
Code UNSPSC :
41106305
ID de substance PubChem :
24893135
Nomenclature NACRES :
NA.51

Pureté

≥95%

Forme

powder

Poids mol.

491.18  g/mol

Température de stockage

−20°C

Chaîne SMILES 

[Na].Nc1ncnc2n(cnc12)C3OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)CC3O

InChI

1S/C10H16N5O12P3.Na.H/c11-8-7-9(13-3-12-8)15(4-14-7)10-6(16)1-5(25-10)2-24-29(20,21)27-30(22,23)26-28(17,18)19;;/h3-6,10,16H,1-2H2,(H,20,21)(H,22,23)(H2,11,12,13)(H2,17,18,19);;

Clé InChI

FRGBONDYLMUOMH-UHFFFAOYSA-N

Description générale

Cordycepin (3′-deoxyadenosine) is a cytotoxic adenosine analog and a bioactive agent extracted from Cordyceps militaris. Cordycepin 5′-triphosphate is a toxic derivative of cordycepin.

Application

Cordycepin 5′-triphosphate sodium salt has been used:
  • as a transcriptional inhibitor in RNA decay assay
  • to inhibit polyadenylation in HEK293T cells before harvesting for in- vitro interaction studies through co-immunoprecipitation (co-Ips)
  • as a positive control in in vitro assays for polymerase inhibition
  • as a precursor to produce cordycepin monophosphate

Actions biochimiques/physiologiques

Cordycepin exhibits various metabolic effects by activating AMP-activated protein kinase (AMPK) in humans. Cordycepin triphosphate inhibits picornavirus polymerase-specific RNA synthesis by blocking in vitro [3H]GMP incorporation. It also retards cell growth by inhibiting RNA synthesis.
Cordycepin 5′-triphosphate is incorporated into nucleic acid by poly(A) polymerase. Because it lacks a 3′-hydroxyl group chain production it can be used for 3′-end labeling of RNA.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Warning

Classification des risques

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Sigma-Aldrich

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Ming Wei Chen et al.
Antiviral research, 143, 38-47 (2017-04-10)
Chikungunya virus (CHIKV) is an important arboviral infectious agent in tropical and subtropical regions, often causing persistent and debilitating disease. The viral enzyme non-structural protein 4 (nsP4), as RNA-dependent RNA polymerase (RdRP), catalyzes the formation of negative-sense, genomic and subgenomic
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Land-use intensification is a major driver of biodiversity loss. Alongside reductions in local species diversity, biotic homogenization at larger spatial scales is of great concern for conservation. Biotic homogenization means a decrease in β-diversity (the compositional dissimilarity between sites). Most
3′-end labeling of RNA with recombinant yeast poly(A) polymerase.
Lingner J, Keller W.
Nucleic Acids Research, 25, 2917-2920 (1993)
D L Panicali et al.
Journal of virology, 25(1), 124-128 (1978-01-01)
Cordycepin triphosphate inhibited in vitro [3H]GMP incorporation by pricornavirus-specific polymerase complexes isolated from infected HeLa cells. The inhibition of [3H]GMP incorporation could be reversed with ATP added to the reaction mixture along with the inhibitor, but not with GTP so
Nicole Montreau et al.
Comptes rendus biologies, 326(12), 1135-1147 (2004-01-30)
Using an in vivo heterologous system to study the stability of Xenopus laevis RNA injected into axolotl (Ambystoma mexicanum) fertilized eggs, we have previously observed unexpected fluctuations in RNA level during early development [Andéol et al., Differentiation 63 (1998) 69-79].
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